(2E)-2-[(3-bromo-4-pyridyl)-methylene]-6-methoxy-tetralin-1-one → 2-[(3-Bromo-4-pyridyl)methyl]-6-methoxy-tetralin-1-one

HRID 2207194Notes

Reaction equation

HRID 2207194 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1/[CH:8]=[C:9]1/[C:10](=[O:21])[C:11]2[C:16]([CH2:17][CH2:18]/1)=[CH:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2>CCO.[Pt]>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21]

Participants

4

Reactant 1

HCID 118557971(2E)-2-[(3-bromo-4-pyridyl)-methylene]-6-methoxy-tetralin-1-one

Product 1

HCID 1185580372-[(3-Bromo-4-pyridyl)methyl]-6-methoxy-tetralin-1-oneYield 99.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Pt/C (5 wt % loading, 200 mg) was added to a stirred solution of the compound 87 (2.0 g, 5.81 mmol) in EtOH (58 mL) at room temperature. The resulting suspension was stirred for 4 hours under H2 atmosphere (1 atm) then filtered over Celite, rinsed with dichloromethane and concentrated to dryness. The crude residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether) to afford the title compound 99 (Yield 2.0 g, 99%).

Workup

  1. filtrationthen filtered over Celite
  2. washrinsed with dichloromethane
  3. concentrationconcentrated to dryness
  4. customThe crude residue was purified by column chromatography on SiO2 (gradient of EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-f281a1d249bd470aaa551745148ce49c
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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